Downtown Sykesville Connection


The Downtown Sykesville Connection exists to preserve, promote, and enhance the character, history, and vibrancy of Downtown Sykesville for all to enjoy

The Downtown Sykesville Connection, Inc (DSC) was awarded the titles of “Coolest Small Town in America” by Budget Travel (2016) and “Best Main Street in America” by Independent We Stand amid the Covid-19 pandemic (2020), highlighting our promotion and marketing program as one of the organization’s strongest assets. A record-setting 1.5 million total votes were cast in the 2020 contest, 160,000 for Sykesville, shy of 4,800 residents. It positioned the DSC as the innovative conductor of new virtual relationships.

The DSC continued to establish its value as the builder of emotional connections between community members or the community and its downtown through the 2016 contest. From the block party announcing Sykesville’s participation to the event celebrating the win, the DSC witnessed Sykesville community pride grow. Our Main Street program has nurtured this sense of pride and belonging ever since, and we still feel it on Main Street today. It is the cornerstone of our identity and a qualitative measure of the validity of the Main Street Program.

The “Coolest and Best” titles represent the recognition of our Main Street organization as an indispensable driver of economic and community development. They have allowed the DSC to establish its brand and continue developing marketing campaigns, programs, and merchandise.

Our Main Street program's success was honored in 2023 when it was selected as a semifinalist for the prestigious Great American Main Street Award. This recognition came from an expert panel at the National Main Street Center, acknowledging our initiative as one of the top eight community and economic development programs out of more than 1,200 across the United States.

Stories That Build Sykesville:
A Tribute to Black Heritage


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Snallygaster Walking Tour

Enjoy our Snallygaster walking tour! Whether you want to find the mini-murals or listen to the book recording, click the button below!

Walking Tour Starts Here!

Join the team! All we need is you!

Whether you enjoy the thrill of event planning and operations or wish to help with fundraising for community programs, whether you prefer brainstorming or are interested in turning Sykesville into a "green town", we have the perfect volunteer opportunity for you.

Volunteer Today!

Store

Our postcards and other products are available at the Visitor Center / Post Office 731 Oklahoma Avenue
Sykesville, MD 21784-7363

Phone: 410-552-9975

Latest News Around Town

🎉 Welcome to the Neighborhood, Uncle Joe’s! 🍗🍞☕There’s a new aroma about to join the delicious scents of downtown — and trust us, it’s worth getting excited about. Uncle Joe’s, a soul...
✨ Spotlight: Moonshadow Collective – A New Creative Hub ... Moonshadow Collective is designed for artists, makers, and creatives of all levels —from seasoned painters to curious beginners. Their s...
🍍Sippin’ on Summer 2025: A Toast to Our Incredible Spons... If you heard music in the air, laughter on Main Street, and the sweet clink of summer cheers , you were definitely near Sippin’ on Summe...

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The DSC was awarded the titles of Coolest Small Town in America by Budget Travel in 2016 and Best Main Street in America by Independent We Stand in 2020. The DSC was also recognized as a semifinalist of the Great American Main Street Award in 2023.

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The Downtown Sykesville Connection recognizes the Town of Sykesville as its partner and lead sponsor.